Winter can get a bit of a bad rap when it comes to trying to dress yourself. Winter in Winnipeg generally can get a bit of a bad rap. And I get it, I do, it’s hard to feel cute or like yourself when every outfit and inch of exposed flesh either has to be tucked under a huge coat or subjected to an icy blast the moment you set food out the door.

But, like most things in life, good can come bundled in with the bad. My friend Amos calls winter “a time for contemplation,” when meticulously putting on each protective layer can feel like a meditative act, and removing them, a catharsis. Elsa adds, “It’s very acceptable to retreat within yourself in the winter time.”

And Winnipeg winters can afford us such opportunities: to cozy up under an extra layer of soft fabric, or assemble new outfits by throwing together pieces we wouldn't pair otherwise. It's cold out there; sometimes you have to get creative. And so, on a chilly Sunday early in December, I’ve gathered a small group of people together at Modern Supply Co. to talk about their sense of style and self expression, and how winter plays into that.

Elsa wears a velour button down from Shop Take Care, a beige bodysuit from Urban Outfitters, jeans from Levi's, boots from Rooster, and jewellery gifted from a friend.

Elsa Taylor: I don’t feel like I really have a personal style, I just try to play it safe and comfortable. My hair is more of a mood ring for me. I switch between warm hair colours or cool ones. It can be any shade in those families, but that’s what I feel the strongest about. One day I’ll go, “This is absolutely not okay anymore! It has to be warm now!” Every couple of months something’s got to give.

This shirt and these Levis are both second-hand from Shop Take Care. I try to check in there every couple of weeks. The shirt reminds me of a purple velvet blazer my mom wore to church every Sunday. I remembered how it smelled, her Ralph Lauren perfume. She’s a professor, and she looked so eccentric and distinguished when she wore it. As an adolescent, I thought she didn’t have style at all, but now I consider her to be the pinnacle of fashion.

When I was younger, I felt like the thing to do was to dress in a very feminine manner. I love all things feminine, but I find that I don’t feel as comfortable wearing feminine clothes anymore. I feel most comfortable wearing soft and flowing layers, lots of black and neutral colours.

In the winter time, I have more of a tough presentation. My summertime aesthetic is softer and more feminine with flowing sundresses. In the winter I wear a lot of denim, layered shirts, and leather jackets. It’s a protective shell. I like to retreat into myself at any opportunity, and winter is a great time for that. I don’t like to feel exposed.

Julia wears a headband from Anthropologies, a pullover from H&M, pants from Shop Take Care, shoes from the Goodwill, and a vest from Tony Chestnut.

Julia Huard: When I’m winter cycling, I have to try to figure out how to put together something that I’m okay with getting dirty. I’m not really someone who buys MECC water proof gear. My boyfriend does it, and he makes it work for him, but it’s not for me. I feel like it would cramp my style.

I got this Tony Chestnut blanket vest about a year ago. I’m not sure what other colours to wear with it, except for black. I tend to wear all black all the time. My family and friends make fun of me for it, so I’m trying to add more diversity in terms of colour to my wardrobe, but I always revert back to all black. That started in high school. I wasn’t a goth kid, but I wore a lot of dark clothing. I feel like it suits my personality. When I wear a lot of vibrant colours, I don’t feel like myself. You get made fun of for the way you dress, and then you internalize it and go, “I have to change,” and you go out and you buy things that don’t really suit you and they end up collecting dust at the back of your closet somewhere.

Colour is very approachable I think. People might assume that you’re more open or friendly. I’m an introverted person. It’s not that I don’t like be approached, I do, but I like to fade into the background most of the time, especially when there’s a crowd.

Elizabeth wears a dress from Calvin Klein, a thrifted cardigan and bag, shoes from Payless, tights from her oma, gloves from her opa, and a coat from Additionelle.

Elizabeth Shearer: I inherited these beautiful leather gloves from my opa, and I’m also wearing some of my oma’s stockings. My oma was quite frugal. When she moved to a smaller place, I found amazing clothes in her closet — floral, two-piece, silk things, and a lot of polyester in beautiful patterns — that she never wore. She’d have them in case there was an event, but she would always go, “No, that’s too good.” She didn’t appear to be a very fancy woman, but going through her closets, she is fancy as hell. I don’t think she is used to being able to spend money and enjoy it. She grew up in Russia and went through the war.

I thrifted this cardigan. It’s been in my closet for six years, and I whip it out every time I want to feel fancy. I have a lot of those kinds of articles in my closet, almost taking after my oma a bit. I’ll have them for years, and I’ll wear something out to a party, and people will go, “Oh, is that new?” And I’ll be like, “I’ve literally had this for ten years.”

I bought this dress for twenty bucks at the Bay. They have plus sizes, and they’re are a lot of fabulous choices. I like that it’s sleeveless. My my mom and aunts will say so casually that they can’t wear things because of their arms. There are different rules that larger women are subject to or think are enforceable.

Payless is the only shoe store I’ve found here that carries size 12 shoes for women. Most stores cut off at size 10. I have a double whammy, being plus size and having larger feet. Sometimes it makes me feel empowered, because I’m not burdened by choice. Growing up, I wasn’t super into fashion because I couldn’t fit into the idea of what fashionable looked like. One of the first times I went shopping and felt empowered was with my dad when he took me shopping for my grade six grad dress. I was already tall. Everyone in my grade would go to Garage Clothing, and I didn’t fit any of that stuff. I just went, “Well, I can’t participate.” My dad took me to women’s clothing stores. There were clothes that I never knew existed, because I’d never had an adult go, “These are possibilities for you.” I picked out this baby-blue paisley summer dress.

I love clothes now, and I find it a really empowering expression of how I’m feeling, as well as a sense of enjoyment. It’s empowering to look the way you want to look. I didn’t know I had access to that when I was younger.

Amos wears a turtleneck and blazer from clothing swaps, a thrifted skirt, leggings from their friend Morag, socks gifted from their brother, and mini platform boots gifted from their dad.

Amos Bridgman: When I assemble an outfit, I like to have all the colours matching and coordinating. I start with whatever covers my legs — pants or a skirt or a dress, and then I build around that. Winter is amazing because I can strip off layers, and I can add them on. I’m a winter cyclist, so there’s a balance between utilitarian efficiency, keeping warm, and how fashionable I want to be.

In the past three or four years, my style has become much more amorphous, constantly transitioning outside of itself and bringing things back in. Right now, I have no idea where my style is going to go, what it’s going to be. There are aspects of masculinity and femininity in my clothes, but that’s more to do with how I will be perceived. I dress according to how I want to feel in my body. Gender plays into that, but I find those are just the beginning points from which to explore those feelings.

I have a fit body that is equated with masculinity, but I don’t necessarily feel masculine. I can wear just a skirt, and people will go, “Nice kilt!” or, “Hey dude! You’re rocking it.” I’m glad that people are accepting, but also this isn’t a kilt, it’s a skirt.

Much of my expression is a gift from a community. When I was younger, my mom would put her arms around me and say, “I’m giving you a circle of protection.” Now, when I feel like I need that, I just put on the clothes that she’s given me or that I’ve taken from her closet. With each of these clothes, comes the person, but it’s not just the memory of the person. When I get overwhelmed, I can touch the piece and go, “This is them.” It’s grounding.

Kali wears a jumpsuit from Vestige, a sweater from Nettie and Min, earrings from Deconstruct, and Converse shoes.

Kali Siemens: I love cozy, soft knits, but I find I’m a lazier dresser in winter. I’ll usually wear a wrinkly sweater and some big, baggy pants. I’m currently wearing a Vestige jumpsuit from the shop. I can’t get out of this thing. It’s just soft, it feels like flannel pyjamas. I’ve worn it on airplanes, I’ve fallen asleep in it. It’s a good, easy piece. I usually throw a big, bulky sweater over it and call it a day.

My style changes often. Most of the time I look for neutral tones, and these days I’m into texture. Owning Modern Supply Co, I’ve seen a lot of materials come and go, and now I can go into H & M or Forever 21 and understand what textures I’m attracted to.

I grew up North Kildonan, kind of a jock, I lived in LuluLemon in high school. I moved to Scotland for a year, and it was eye opening to me. A lot of girls I met had a punky style - band tees, bold lip, eye liner. I liked less traditionally feminine way of dressing. I also did a circuit through South East Asia where my bag was stolen. During that time, I lived in the t-shirt and jeans I had on. It taught me about minimalism.

I’m drawn to simple things that look good, drape well, that I can do things like run after my kids and go skateboarding in. I’m not necessarily only drawn to masculine clothes. I think the drape of something can be feminine, but I’m not really drawn to the tight clothing I used to associate with feminine dressing.

If I’m wearing a nice dress, people will go, “Oh, you look really feminine. It’s kind of counteracting your tattoos.” Women will ask me how I can walk around with that all over my skin. I’ve had someone say, “Don’t you take yourself seriously enough not to ruin your own physique?” And that’s the thing, I don’t. I feel like this is a journal I can see on my body. My first tattoo was inspired by a painting a saw in Scotland — I met my best friend in front of that painting — but a lot of my tattoos don’t have a particular meaning. It might be something funny, or connected to a situation I’m in. I find it’s just a good way to remember events in my life. I don’t care what people say about them anymore.

Karen wears a wrap dress and sweater from Modern Supply Co., jeans from Club Monaco, boots from Zara, and jewellery either gifted or purchased while visiting India.

Karen Sharma: I bought this necklace in India, when I was travelling to visit my family. I also wear three items that I’ve inherited at all times — my dad’s ring, my maternal grandmother’s bracelet, and my paternal grandmother’s ring. Gold bangles tend to be passed on from generation to generation in my culture.

I wear a lot of black and darker tones. I’m very drawn to texture. I bought my pants because they’re really soft. I like my clothes to reflect my identities, so I like things that have a bit of edge to them and reflect my queerness. I try to keep pieces of my cultural identity and personhood as a South Asian on my body. I wear a lot of kurtas — long tops traditionally worn by men in India — as part of my fashion.

It took me awhile to come into a queer femme identity. I spent a lot of time trying to play with androgyny, but in the last five or six years I’ve settled into feeling comfortable as a queer femme person. Clothes are so much a part of that, because you deal with a lot of non-recognition and invisibility when you’re femme. Finding clothes that imprint their queerness on me or let me imprint my queerness on the world has been really important, and has taken some time. That also means constantly battling people who don’t want to take me seriously. I think sometimes people read queerness as youthfulness, and don’t give it the kind of respect that it ought to be given.

I like wearing the same pieces throughout the year, but finding different uses for them. I wear this apron dress year round, I just wear it differently depending on the time of year. In winter, I’ll wear sweaters over top or long shirts under it. In the summer, I’ll wear it on its own or with a short sleeve shirt underneath. I like the challenge of keeping a really simple, steady wardrobe and trying to reinvent it through the seasons.

I need to find ways to pull my people up a bit more through what I wear. A lot of the time they’ve been designed by white folk, and then created on the backs of or through the subjugation of people of colour. I would love to do something about that. Every day that I get dressed, I’m clothing a politicized body. The choices I make in acquiring clothes and putting them on my body is a political act. I’m trying to be more aware of the ethics of what I’m doing in addition to how a present myself to the world.

A huge thank you to Kali for opening her store to us, and to all the people who took the time and consideration to talk and make photographs with me. A quick reminder that this time of year can be challenging for people who don't have a steady home or can't afford a good winter coat. Donations of gently used winter gear to shelters, family and resource centres, and newcomer organizations are always welcome.